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In Top Five, Chris Rock’s new film and third attempt at writing and directing, the worlds of stand-up comedy, reality TV and addiction collide in what turns out to be a riotous and surprisingly heartfelt comedy. Rock has had mixed results as a movie star and holds an even spottier resume as a writer-director (he previously sat in the big chair for 2000’s Head of State and 2007’s I Think I Love My Wife), but the third time seems to be the charm for the former “Saturday Night Live” star.

In Top Five, Rock plays Andre Allen; a comedian fighting to be taken seriously as he enters the next phase of his uber-successful Hollywood career. After launching the lucrative “Hammy the Bear” franchise, Allen is now attempting a dramatic epic about a Haitian slave uprising, while also obsessing over his upcoming marriage to reality star Erica Long (Gabrielle Union). Rock’s perspective on what it’s like to be a successful Black comic that still gets pigeonholed by the industry and the fans echoes not only his career, but what most funnymen face once they become superstars.

Rosario Dawson is excellent as Chelsea Brown, a reporter from the New Yorker who’s followed Allen’s entire career and spends a day with him as he revisits his old stomping grounds around New York City. The actress does an excellent job of keeping Brown’s character from becoming either too much of a fly-on-the-wall in the story or too much of an idealized “grounded girl that helps the troubled celebrity find himself” cliche. The all-star cast includes other titans of comedy such as Cedric the Entertainer (who gets to go to outrageous extremes as promoter Jazzy D), Kevin Hart and Jerry Seinfeld. Most of the appearances work well, never feeling contrived or  calculated; and it fits well with a movie so intent at examining the cost of fame and the troubles of the famous.

Beyond the observations about celebrity, however, Top Five offers the best cinematic version of Chris Rock’s perspective. Ruminations on rap, race and relationships are embedded into virtually every facet of the film; from the plot to the cameos. When Rock hangs out with his family in the projects, their arguments about their top five rappers feel real and effortless; as opposed to shoehorned in to remind audiences that the filmmaker is of the hip-hop generation.

That isn’t to say that Top Five always hits the mark; some of the jokes tend to run on a minute too long and it occasionally slips into predictability. Union’s character rarely rises above Kardashian-esque caricature — though she does try to keep the demanding diva from becoming too outlandish. And one can’t help but wish there was a bit more screen time for the venerable Ben Vereen; who shines as Andre’s bitter father, struggling to come to grips with the fact that his son made more of a life for himself than he ever did.

But Chris Rock succeeds in telling a quintessentially New York story while also managing to skewer Hollywood with the kind of perceptiveness that has informed his best stand-up material. It’s hard to believe that the guy who directed Head of State was able to put this together. Here’s hoping he only gets better.

Stereo Williams

Todd “Stereo” Williams, entertainment writer based in New York City. He co-founded Thirty 2 Oh 1 Productions, an indie film company.